FI863592A0 - ISOLERING AV ICKE-REDUCERADE OLIGOSACKARIDER. - Google Patents
ISOLERING AV ICKE-REDUCERADE OLIGOSACKARIDER.Info
- Publication number
- FI863592A0 FI863592A0 FI863592A FI863592A FI863592A0 FI 863592 A0 FI863592 A0 FI 863592A0 FI 863592 A FI863592 A FI 863592A FI 863592 A FI863592 A FI 863592A FI 863592 A0 FI863592 A0 FI 863592A0
- Authority
- FI
- Finland
- Prior art keywords
- hydrazone derivative
- unreduced oligosaccharides
- oligosaccharides
- unreduced
- reducerade
- Prior art date
Links
- 150000002482 oligosaccharides Chemical class 0.000 abstract 6
- 229920001542 oligosaccharide Polymers 0.000 abstract 4
- 150000007857 hydrazones Chemical class 0.000 abstract 3
- 102000003886 Glycoproteins Human genes 0.000 abstract 2
- 108090000288 Glycoproteins Proteins 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 230000006181 N-acylation Effects 0.000 abstract 1
- 238000007171 acid catalysis Methods 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 239000001913 cellulose Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000003776 cleavage reaction Methods 0.000 abstract 1
- 238000004440 column chromatography Methods 0.000 abstract 1
- 239000000356 contaminant Substances 0.000 abstract 1
- 238000006698 hydrazinolysis reaction Methods 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000007017 scission Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
- C07K9/001—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence having less than 12 amino acids and not being part of a ring structure
- C07K9/005—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence having less than 12 amino acids and not being part of a ring structure containing within the molecule the substructure with m, n > 0 and m+n > 0, A, B, D, E being heteroatoms; X being a bond or a chain, e.g. muramylpeptides
-
- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K13/00—Sugars not otherwise provided for in this class
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Health & Medical Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Saccharide Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Respiratory Apparatuses And Protective Means (AREA)
- Catching Or Destruction (AREA)
- Polyesters Or Polycarbonates (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Noodles (AREA)
- Spark Plugs (AREA)
Abstract
A preparative scale method for the isolation of unreduced oligosaccharides of glycoproteins and glycohormones having a N-linked oligosaccharide structure is disclosed. The method employs hydrazinolysis of the glycoprotein or glycohormone under reaction conditions to cause cleavage at the N-linked sites, producing a mixture having as a major component a de-N-acetylated hydrazone derivative of the oligosaccharides, followed by N-acylation of the hydrazone derivative, acid-catalysis of the hydrazone derivative to produce unreduced oligosaccharides, and subjecting the resulting unreduced oligosaccharides to cellulose column chromatography to remove contaminants and to recover the unreduced oligosaccharides.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/772,988 US4719294A (en) | 1985-09-06 | 1985-09-06 | Isolation of unreduced oligosaccharides |
US77298885 | 1985-09-06 |
Publications (4)
Publication Number | Publication Date |
---|---|
FI863592A0 true FI863592A0 (en) | 1986-09-05 |
FI863592A FI863592A (en) | 1987-03-07 |
FI83962B FI83962B (en) | 1991-06-14 |
FI83962C FI83962C (en) | 1991-09-25 |
Family
ID=25096828
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI863592A FI83962C (en) | 1985-09-06 | 1986-09-05 | Isolation of non-reduced oligosaccharides |
Country Status (14)
Country | Link |
---|---|
US (2) | US4719294A (en) |
EP (1) | EP0215766B1 (en) |
JP (1) | JPS6263524A (en) |
AT (1) | ATE68213T1 (en) |
AU (1) | AU580686B2 (en) |
CA (1) | CA1266265A (en) |
DE (1) | DE3681865D1 (en) |
DK (1) | DK425186A (en) |
FI (1) | FI83962C (en) |
GR (1) | GR862279B (en) |
IE (1) | IE59088B1 (en) |
IL (1) | IL79953A0 (en) |
NO (1) | NO164478C (en) |
ZA (1) | ZA866774B (en) |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3528654A1 (en) * | 1985-08-09 | 1987-02-19 | Hoechst Ag | METHOD FOR PRODUCING ALKYLATED HYDROXYL GROUP-FREE GLYCOSYL FLUORIDES |
US4719294A (en) * | 1985-09-06 | 1988-01-12 | Monsanto Company | Isolation of unreduced oligosaccharides |
US5324828A (en) * | 1986-12-11 | 1994-06-28 | Genzyme Corporation | 1-amino-1-deoxyoligosaccharides and derivatives thereof |
EP0606925B1 (en) * | 1986-12-11 | 1998-10-07 | Genzyme Corporation | A method for derivatizing a 1-amino-1-deoxyoligosaccharide |
US5344870A (en) * | 1987-12-02 | 1994-09-06 | Alberta Research Council | Sialic acid glycosides, antigens, immunoadsorbents, and methods for their preparation |
US5079353A (en) * | 1987-12-02 | 1992-01-07 | Chembiomed, Ltd. | Sialic acid glycosides, antigens, immunoadsorbents, and methods for their preparation |
DE3923365A1 (en) * | 1989-07-14 | 1991-01-24 | Suedzucker Ag | OLIGOSACCHARIDALDITOLS WITH AMIDE BINDING AND METHOD FOR THE PRODUCTION THEREOF |
US5422079A (en) * | 1990-06-21 | 1995-06-06 | Oxford Glycosystems Limited | Automated process equipment |
DE69130136T2 (en) * | 1990-06-21 | 1999-03-11 | Oxford Glycosciences (Uk) Ltd., Abingdon, Oxon | Automated process for the splitting of biomolecules |
GB9013831D0 (en) * | 1990-06-21 | 1990-08-15 | Oxford Glycosystems Ltd | Release and isolation of unreduced'n-linked type'oligosaccharides |
EP0462795A3 (en) * | 1990-06-21 | 1993-02-24 | Oxford Glycosystems Limited | Isolation of glycans |
GB9013830D0 (en) * | 1990-06-21 | 1990-08-15 | Oxford Glycosystems Ltd | Release and isolation of unreduced'o-linked type'oligosaccharides |
GB9013828D0 (en) * | 1990-06-21 | 1990-08-15 | Oxford Glycosystems Ltd | Release and isolation of unreduced'n-and o-linked type'oligosaccharides |
DK0649427T3 (en) * | 1992-06-01 | 1998-03-02 | Biomembrane Inst | Sequential removal of monosaccharides from the reducing end of oligosaccharides and applications thereof |
US5411892A (en) * | 1993-08-13 | 1995-05-02 | University Of Washington | Method and apparatus for carbohydrate analysis |
US5585473A (en) * | 1994-12-09 | 1996-12-17 | The Biomembrane Institute | Compounds and methods for monosaccharide analysis |
WO2002012254A1 (en) * | 2000-08-02 | 2002-02-14 | Takara Bio Inc. | Process for producing hydrazinomonosaccharide derivatives and use thereof |
US20040096933A1 (en) * | 2002-11-15 | 2004-05-20 | Yunping Huang | Method of preparation of oligosaccharides |
US20040096948A1 (en) * | 2002-11-15 | 2004-05-20 | Yunping Huang | Glycoprotein cleavage protocol for oligosaccharide analysis |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4362720A (en) * | 1977-04-14 | 1982-12-07 | Chembiomed Ltd. | Synthesis of 2-amino-2-deoxyglycoses and 2-amino-2-deoxyglycosides from glycals |
US4719294A (en) * | 1985-09-06 | 1988-01-12 | Monsanto Company | Isolation of unreduced oligosaccharides |
-
1985
- 1985-09-06 US US06/772,988 patent/US4719294A/en not_active Expired - Lifetime
-
1986
- 1986-09-05 JP JP61209417A patent/JPS6263524A/en active Granted
- 1986-09-05 DE DE8686870123T patent/DE3681865D1/en not_active Expired - Lifetime
- 1986-09-05 AU AU62358/86A patent/AU580686B2/en not_active Ceased
- 1986-09-05 AT AT86870123T patent/ATE68213T1/en not_active IP Right Cessation
- 1986-09-05 FI FI863592A patent/FI83962C/en not_active IP Right Cessation
- 1986-09-05 DK DK425186A patent/DK425186A/en not_active Application Discontinuation
- 1986-09-05 ZA ZA866774A patent/ZA866774B/en unknown
- 1986-09-05 CA CA000517634A patent/CA1266265A/en not_active Expired - Lifetime
- 1986-09-05 IL IL79953A patent/IL79953A0/en not_active IP Right Cessation
- 1986-09-05 EP EP86870123A patent/EP0215766B1/en not_active Expired - Lifetime
- 1986-09-05 GR GR862279A patent/GR862279B/en unknown
- 1986-09-05 IE IE237186A patent/IE59088B1/en not_active IP Right Cessation
- 1986-09-05 NO NO863564A patent/NO164478C/en unknown
- 1986-11-12 US US06/929,962 patent/US4736022A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
EP0215766A3 (en) | 1988-07-27 |
CA1266265C (en) | 1990-02-27 |
DE3681865D1 (en) | 1991-11-14 |
FI83962C (en) | 1991-09-25 |
JPS6263524A (en) | 1987-03-20 |
ATE68213T1 (en) | 1991-10-15 |
US4736022A (en) | 1988-04-05 |
FI83962B (en) | 1991-06-14 |
US4719294A (en) | 1988-01-12 |
NO863564L (en) | 1987-03-09 |
NO164478C (en) | 1990-10-10 |
IE59088B1 (en) | 1994-01-12 |
AU6235886A (en) | 1987-03-12 |
JPH0579079B2 (en) | 1993-11-01 |
NO164478B (en) | 1990-07-02 |
ZA866774B (en) | 1987-07-29 |
NO863564D0 (en) | 1986-09-05 |
IL79953A0 (en) | 1986-12-31 |
GR862279B (en) | 1987-01-12 |
CA1266265A (en) | 1990-02-27 |
AU580686B2 (en) | 1989-01-27 |
DK425186D0 (en) | 1986-09-05 |
IE862371L (en) | 1987-03-06 |
FI863592A (en) | 1987-03-07 |
DK425186A (en) | 1987-03-07 |
EP0215766A2 (en) | 1987-03-25 |
EP0215766B1 (en) | 1991-10-09 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM | Patent lapsed | ||
MM | Patent lapsed |
Owner name: MONSANTO COMPANY |